Hydrochloric Acid → HCID 23366923, compound

HRID 1079386Notes

Reaction equation

HRID 1079386 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([O:20][CH:21]3[CH2:26][CH2:25][N:24]([C:27](=[O:29])[CH3:28])[CH2:23][CH2:22]3)[CH:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[ClH:30]>C(O)C>[ClH:30].[C:27]([N:24]1[CH2:23][CH2:22][CH:21]([O:20][C:13]2[CH:12]=[C:11]([O:10][CH:7]3[CH2:6][CH2:5][N:4]([C:1](=[O:3])[CH3:2])[CH2:9][CH2:8]3)[CH:16]=[CH:15][C:14]=2[NH2:17])[CH2:26][CH2:25]1)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23366917HCID 23366917, compound

Product 1

HCID 23366923HCID 23366923, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,3-Di(1-acetyl-4-piperidyloxy)-4-nitrobenzene (3.7 g) was dissolved in a mixed solution of ethanol (30 ml) and conc. hydrochloric acid (1 ml) and then catalytic reduction was conducted according to the same manner as that described in Example 1, (2). After completion of the reaction, the catalyst was removed and then the solvent was distilled off to obtain 2,4-di(1-acetyl-4-piperidyloxy)aniline hydrochloride (3.9 g) as an amorphous solid. The amorphous solid (1.23 g) was dissolved in dimethylformamide (5 ml) and potassium carbonate (1.24 g) and 1,4-dibromobutane (0.36 ml) were added to the mixture, which was heated with stirring at 100° C. for one hour. After completion of the reaction, water (50 ml) was added to the reaction mixture, which was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then the solvent was distilled off. The residual oily compound was separated and purified by silica gel column chromatography (developing solvent: methanol/dichloroethane=1/19 (v/v)) to obtain an oily compound (0.9 g).

Workup

  1. customAfter completion of the reaction
  2. customthe catalyst was removed
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-cf5b4f88b56643219c742cce3bb88bdf
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

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